# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_new1 #TrackingRef '12377_web_deposit_cif_file_1_JustynaKalinowska-Tluscik_1341322378.ccdc_deposit_OK2_KO3.cif' _audit_creation_date 2012-06-26T14:59:54-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (E)-3-[(3-hydroxypropylamino)-phenylmethylidene]-1,3-dihydro-2H- 1-phenylpyrido[2,3-b]pyrrolo[2,3-e]pyrazin-2-one monohydrate ; _chemical_name_common 'Compound KO3' _chemical_formula_moiety 'C25 H21 N5 O2, H2 O' _chemical_formula_sum 'C25 H23 N5 O3' _chemical_formula_weight 441.48 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2202(2) _cell_length_b 6.1966(4) _cell_length_c 31.8009(10) _cell_angle_alpha 90 _cell_angle_beta 109.409(2) _cell_angle_gamma 90 _cell_volume 2085.48(15) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 7822 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; DENZO-SMN; Otwinowski & Minor, 1997 ; _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9971 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.0199207 _diffrn_orient_matrix_ub_12 -0.0052391 _diffrn_orient_matrix_ub_13 -0.0330545 _diffrn_orient_matrix_ub_21 -0.1519423 _diffrn_orient_matrix_ub_22 0.0275074 _diffrn_orient_matrix_ub_23 -0.0043542 _diffrn_orient_matrix_ub_31 0.0505958 _diffrn_orient_matrix_ub_32 0.084634 _diffrn_orient_matrix_ub_33 0.0001327 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_unetI/netI 0.0528 _diffrn_reflns_number 14239 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.7 _diffrn_reflns_theta_max 27.41 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 4696 _reflns_number_gt 3177 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1006P)^2^+1.2247P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.011(2) _refine_ls_number_reflns 4696 _refine_ls_number_parameters 313 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1859 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.482 _refine_diff_density_min -0.603 _refine_diff_density_rms 0.072 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.61623(15) 0.3156(3) 0.43283(6) 0.0292(4) Uani 1 1 d . . . N4 N 0.39313(17) 0.8652(3) 0.33076(6) 0.0230(5) Uani 1 1 d . . . N5 N 0.35855(18) 1.1827(3) 0.29038(7) 0.0257(5) Uani 1 1 d . . . N9 N 0.66318(18) 0.9360(3) 0.35670(7) 0.0248(5) Uani 1 1 d . . . N30 N 0.23923(18) 0.5387(4) 0.34861(7) 0.0261(5) Uani 1 1 d . . . H30 H 0.251(3) 0.629(5) 0.3304(10) 0.035(8) Uiso 1 1 d . . . C9A C 0.6121(2) 0.7783(4) 0.37139(7) 0.0228(5) Uani 1 1 d . . . C4A C 0.4434(2) 1.0418(4) 0.31663(7) 0.0221(5) Uani 1 1 d . . . N1 N 0.67320(17) 0.6164(3) 0.39998(7) 0.0244(5) Uani 1 1 d . . . O39 O -0.1174(2) 0.5728(4) 0.26146(8) 0.0539(6) Uani 1 1 d D . . H39 H -0.197(2) 0.601(9) 0.2465(16) 0.120(19) Uiso 1 1 d D . . C8 C 0.6178(2) 1.2570(4) 0.31214(8) 0.0265(6) Uani 1 1 d . . . H8 H 0.7058 1.281 0.3186 0.032 Uiso 1 1 calc R . . C3A C 0.4768(2) 0.7395(4) 0.35898(7) 0.0221(5) Uani 1 1 d . . . C8A C 0.5759(2) 1.0755(4) 0.32879(8) 0.0236(5) Uani 1 1 d . . . C2 C 0.5839(2) 0.4718(4) 0.40855(8) 0.0239(5) Uani 1 1 d . . . C6 C 0.4026(2) 1.3590(4) 0.27635(8) 0.0276(6) Uani 1 1 d . . . H6 H 0.3434 1.4605 0.2588 0.033 Uiso 1 1 calc R . . C11 C 0.8076(2) 0.5983(4) 0.42013(8) 0.0238(5) Uani 1 1 d . . . C31 C 0.3297(2) 0.3043(4) 0.41285(8) 0.0224(5) Uani 1 1 d . . . C3 C 0.4590(2) 0.5534(4) 0.38253(8) 0.0231(5) Uani 1 1 d . . . C37 C 0.1068(2) 0.4850(4) 0.34081(9) 0.0290(6) Uani 1 1 d . . . H37A H 0.0988 0.4108 0.3673 0.035 Uiso 1 1 calc R . . H37B H 0.0761 0.3858 0.3151 0.035 Uiso 1 1 calc R . . C36 C 0.3745(2) 0.3559(4) 0.45828(8) 0.0266(6) Uani 1 1 d . . . H36 H 0.41 0.4942 0.4677 0.032 Uiso 1 1 calc R . . C14 C 1.0665(2) 0.5665(5) 0.45921(9) 0.0313(6) Uani 1 1 d . . . H14 H 1.1555 0.5553 0.4729 0.038 Uiso 1 1 calc R . . C30 C 0.3410(2) 0.4664(4) 0.38007(8) 0.0222(5) Uani 1 1 d . . . C13 C 0.9978(2) 0.3901(5) 0.43816(9) 0.0307(6) Uani 1 1 d . . . H13 H 1.0398 0.258 0.4372 0.037 Uiso 1 1 calc R . . C7 C 0.5312(2) 1.4016(4) 0.28623(8) 0.0279(6) Uani 1 1 d . . . H7 H 0.5584 1.5283 0.2753 0.033 Uiso 1 1 calc R . . C16 C 0.8758(2) 0.7771(4) 0.44111(8) 0.0265(6) Uani 1 1 d . . . H16 H 0.8341 0.9093 0.4422 0.032 Uiso 1 1 calc R . . C12 C 0.8669(2) 0.4040(4) 0.41823(8) 0.0270(6) Uani 1 1 d . . . H12 H 0.8192 0.2826 0.4036 0.032 Uiso 1 1 calc R . . C32 C 0.2769(2) 0.1021(4) 0.39959(8) 0.0256(5) Uani 1 1 d . . . H32 H 0.2445 0.0667 0.3688 0.031 Uiso 1 1 calc R . . C33 C 0.2714(2) -0.0470(4) 0.43103(9) 0.0288(6) Uani 1 1 d . . . H33 H 0.2363 -0.1855 0.4218 0.035 Uiso 1 1 calc R . . C35 C 0.3672(2) 0.2058(5) 0.48957(8) 0.0297(6) Uani 1 1 d . . . H35 H 0.3968 0.2421 0.5203 0.036 Uiso 1 1 calc R . . C15 C 1.0064(2) 0.7603(5) 0.46057(8) 0.0295(6) Uani 1 1 d . . . H15 H 1.0544 0.8821 0.4748 0.035 Uiso 1 1 calc R . . C34 C 0.3169(2) 0.0035(4) 0.47627(9) 0.0286(6) Uani 1 1 d . . . H34 H 0.3135 -0.1004 0.4978 0.034 Uiso 1 1 calc R . . C39 C -0.1104(3) 0.6456(6) 0.30521(10) 0.0434(7) Uani 1 1 d . . . H39A H -0.1449 0.5341 0.3203 0.052 Uiso 1 1 calc R . . H39B H -0.1605 0.7793 0.3029 0.052 Uiso 1 1 calc R . . C38 C 0.0268(2) 0.6882(5) 0.33160(10) 0.0393(7) Uani 1 1 d . . . H38A H 0.0322 0.7564 0.3603 0.047 Uiso 1 1 calc R . . H38B H 0.0616 0.7912 0.3149 0.047 Uiso 1 1 calc R . . O1W O 0.1248(3) 0.6227(5) 0.24354(11) 0.0699(8) Uani 1 1 d D . . H1W H 0.141(4) 0.765(4) 0.2424(18) 0.105 Uiso 1 1 d D . . H2W H 0.043(2) 0.621(7) 0.2439(16) 0.105 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0217(8) 0.0318(10) 0.0317(10) 0.0100(8) 0.0056(7) 0.0015(7) N4 0.0189(9) 0.0269(11) 0.0214(10) 0.0002(8) 0.0043(8) 0.0001(8) N5 0.0254(10) 0.0274(11) 0.0231(10) 0.0003(9) 0.0065(8) 0.0024(9) N9 0.0202(9) 0.0279(11) 0.0238(10) 0.0014(9) 0.0040(8) -0.0018(9) N30 0.0197(10) 0.0321(12) 0.0240(10) 0.0058(9) 0.0040(8) -0.0021(9) C9A 0.0191(11) 0.0251(13) 0.0219(11) -0.0008(10) 0.0038(9) -0.0004(10) C4A 0.0215(11) 0.0240(13) 0.0197(11) 0.0005(10) 0.0054(9) 0.0001(10) N1 0.0164(9) 0.0280(11) 0.0257(10) 0.0049(9) 0.0030(8) -0.0005(8) O39 0.0362(12) 0.0624(16) 0.0495(13) -0.0102(12) -0.0040(10) 0.0095(11) C8 0.0231(12) 0.0297(14) 0.0254(12) -0.0006(11) 0.0063(10) -0.0062(10) C3A 0.0182(11) 0.0275(13) 0.0200(11) -0.0010(10) 0.0056(9) 0.0002(10) C8A 0.0227(11) 0.0265(13) 0.0198(11) -0.0013(10) 0.0046(9) 0.0003(10) C2 0.0189(11) 0.0297(14) 0.0225(11) 0.0003(10) 0.0060(9) -0.0008(10) C6 0.0322(13) 0.0269(14) 0.0226(12) 0.0018(10) 0.0074(10) 0.0026(11) C11 0.0170(10) 0.0311(14) 0.0223(11) 0.0038(10) 0.0052(9) 0.0010(10) C31 0.0141(10) 0.0269(13) 0.0250(12) 0.0028(10) 0.0051(9) 0.0001(9) C3 0.0189(11) 0.0274(13) 0.0214(11) 0.0011(10) 0.0045(9) -0.0017(10) C37 0.0173(11) 0.0362(15) 0.0294(13) 0.0042(11) 0.0021(10) -0.0027(11) C36 0.0199(11) 0.0301(14) 0.0268(13) -0.0004(11) 0.0036(10) -0.0021(10) C14 0.0175(11) 0.0425(16) 0.0330(14) 0.0095(12) 0.0073(10) 0.0016(11) C30 0.0188(11) 0.0241(13) 0.0224(11) -0.0018(10) 0.0051(9) -0.0002(9) C13 0.0246(12) 0.0356(15) 0.0333(14) 0.0076(12) 0.0115(11) 0.0058(11) C7 0.0330(13) 0.0262(13) 0.0241(12) 0.0015(10) 0.0090(10) -0.0042(11) C16 0.0213(11) 0.0289(14) 0.0280(12) 0.0040(11) 0.0064(10) -0.0005(10) C12 0.0242(12) 0.0293(14) 0.0259(12) 0.0031(10) 0.0060(10) 0.0006(10) C32 0.0213(11) 0.0306(14) 0.0246(12) -0.0024(10) 0.0072(9) -0.0007(10) C33 0.0257(12) 0.0249(13) 0.0367(14) 0.0006(11) 0.0116(11) -0.0027(10) C35 0.0241(12) 0.0393(16) 0.0233(12) 0.0009(11) 0.0049(10) -0.0010(11) C15 0.0200(11) 0.0362(15) 0.0291(13) 0.0029(11) 0.0037(10) -0.0051(11) C34 0.0221(12) 0.0312(14) 0.0315(13) 0.0084(11) 0.0074(10) 0.0024(11) C39 0.0291(14) 0.055(2) 0.0426(17) -0.0002(15) 0.0069(12) 0.0018(14) C38 0.0265(13) 0.0457(18) 0.0418(16) -0.0010(14) 0.0061(12) 0.0021(13) O1W 0.0612(16) 0.0647(18) 0.083(2) 0.0039(16) 0.0232(15) 0.0079(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C2 1.216(3) . ? N4 C3A 1.317(3) . ? N4 C4A 1.373(3) . ? N5 C6 1.336(3) . ? N5 C4A 1.355(3) . ? N9 C9A 1.296(3) . ? N9 C8A 1.385(3) . ? N30 C30 1.322(3) . ? N30 C37 1.462(3) . ? N30 H30 0.85(3) . ? C9A N1 1.374(3) . ? C9A C3A 1.456(3) . ? C4A C8A 1.421(3) . ? N1 C11 1.433(3) . ? N1 C2 1.436(3) . ? O39 C39 1.440(4) . ? O39 H39 0.88(2) . ? C8 C7 1.377(4) . ? C8 C8A 1.390(4) . ? C8 H8 0.95 . ? C3A C3 1.425(3) . ? C2 C3 1.461(3) . ? C6 C7 1.396(4) . ? C6 H6 0.95 . ? C11 C16 1.386(4) . ? C11 C12 1.386(4) . ? C31 C32 1.391(3) . ? C31 C36 1.400(3) . ? C31 C30 1.483(3) . ? C3 C30 1.407(3) . ? C37 C38 1.517(4) . ? C37 H37A 0.99 . ? C37 H37B 0.99 . ? C36 C35 1.384(4) . ? C36 H36 0.95 . ? C14 C13 1.376(4) . ? C14 C15 1.385(4) . ? C14 H14 0.95 . ? C13 C12 1.396(3) . ? C13 H13 0.95 . ? C7 H7 0.95 . ? C16 C15 1.392(3) . ? C16 H16 0.95 . ? C12 H12 0.95 . ? C32 C33 1.377(4) . ? C32 H32 0.95 . ? C33 C34 1.393(4) . ? C33 H33 0.95 . ? C35 C34 1.382(4) . ? C35 H35 0.95 . ? C15 H15 0.95 . ? C34 H34 0.95 . ? C39 C38 1.512(4) . ? C39 H39A 0.99 . ? C39 H39B 0.99 . ? C38 H38A 0.99 . ? C38 H38B 0.99 . ? O1W H1W 0.906(19) . ? O1W H2W 0.916(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3A N4 C4A 114.65(19) . . ? C6 N5 C4A 118.1(2) . . ? C9A N9 C8A 113.5(2) . . ? C30 N30 C37 128.7(2) . . ? C30 N30 H30 117(2) . . ? C37 N30 H30 115(2) . . ? N9 C9A N1 127.3(2) . . ? N9 C9A C3A 124.9(2) . . ? N1 C9A C3A 107.7(2) . . ? N5 C4A N4 115.7(2) . . ? N5 C4A C8A 122.0(2) . . ? N4 C4A C8A 122.3(2) . . ? C9A N1 C11 124.9(2) . . ? C9A N1 C2 110.80(18) . . ? C11 N1 C2 124.2(2) . . ? C39 O39 H39 100(4) . . ? C7 C8 C8A 119.5(2) . . ? C7 C8 H8 120.2 . . ? C8A C8 H8 120.2 . . ? N4 C3A C3 130.1(2) . . ? N4 C3A C9A 122.0(2) . . ? C3 C3A C9A 107.9(2) . . ? N9 C8A C8 119.5(2) . . ? N9 C8A C4A 122.4(2) . . ? C8 C8A C4A 118.1(2) . . ? O2 C2 N1 122.5(2) . . ? O2 C2 C3 131.5(2) . . ? N1 C2 C3 106.0(2) . . ? N5 C6 C7 123.3(2) . . ? N5 C6 H6 118.3 . . ? C7 C6 H6 118.3 . . ? C16 C11 C12 121.3(2) . . ? C16 C11 N1 118.9(2) . . ? C12 C11 N1 119.8(2) . . ? C32 C31 C36 119.3(2) . . ? C32 C31 C30 121.6(2) . . ? C36 C31 C30 119.0(2) . . ? C30 C3 C3A 125.1(2) . . ? C30 C3 C2 127.3(2) . . ? C3A C3 C2 107.6(2) . . ? N30 C37 C38 110.3(2) . . ? N30 C37 H37A 109.6 . . ? C38 C37 H37A 109.6 . . ? N30 C37 H37B 109.6 . . ? C38 C37 H37B 109.6 . . ? H37A C37 H37B 108.1 . . ? C35 C36 C31 120.1(2) . . ? C35 C36 H36 119.9 . . ? C31 C36 H36 119.9 . . ? C13 C14 C15 120.3(2) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? N30 C30 C3 118.2(2) . . ? N30 C30 C31 120.5(2) . . ? C3 C30 C31 121.3(2) . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C8 C7 C6 118.9(2) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C11 C16 C15 119.1(2) . . ? C11 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C11 C12 C13 118.8(2) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C33 C32 C31 120.1(2) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C34 120.7(2) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C34 C35 C36 120.4(2) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C14 C15 C16 120.2(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C35 C34 C33 119.5(2) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? O39 C39 C38 108.1(2) . . ? O39 C39 H39A 110.1 . . ? C38 C39 H39A 110.1 . . ? O39 C39 H39B 110.1 . . ? C38 C39 H39B 110.1 . . ? H39A C39 H39B 108.4 . . ? C39 C38 C37 113.0(3) . . ? C39 C38 H38A 109 . . ? C37 C38 H38A 109 . . ? C39 C38 H38B 109 . . ? C37 C38 H38B 109 . . ? H38A C38 H38B 107.8 . . ? H1W O1W H2W 103(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8A N9 C9A N1 -179.0(2) . . . . ? C8A N9 C9A C3A 2.8(3) . . . . ? C6 N5 C4A N4 178.9(2) . . . . ? C6 N5 C4A C8A -0.9(3) . . . . ? C3A N4 C4A N5 -174.9(2) . . . . ? C3A N4 C4A C8A 4.9(3) . . . . ? N9 C9A N1 C11 2.3(4) . . . . ? C3A C9A N1 C11 -179.3(2) . . . . ? N9 C9A N1 C2 179.8(2) . . . . ? C3A C9A N1 C2 -1.7(3) . . . . ? C4A N4 C3A C3 175.4(2) . . . . ? C4A N4 C3A C9A -4.2(3) . . . . ? N9 C9A C3A N4 0.4(4) . . . . ? N1 C9A C3A N4 -178.1(2) . . . . ? N9 C9A C3A C3 -179.3(2) . . . . ? N1 C9A C3A C3 2.2(3) . . . . ? C9A N9 C8A C8 177.3(2) . . . . ? C9A N9 C8A C4A -2.1(3) . . . . ? C7 C8 C8A N9 -176.7(2) . . . . ? C7 C8 C8A C4A 2.7(3) . . . . ? N5 C4A C8A N9 178.0(2) . . . . ? N4 C4A C8A N9 -1.8(4) . . . . ? N5 C4A C8A C8 -1.4(3) . . . . ? N4 C4A C8A C8 178.8(2) . . . . ? C9A N1 C2 O2 179.8(2) . . . . ? C11 N1 C2 O2 -2.7(4) . . . . ? C9A N1 C2 C3 0.5(3) . . . . ? C11 N1 C2 C3 178.1(2) . . . . ? C4A N5 C6 C7 2.0(4) . . . . ? C9A N1 C11 C16 49.4(3) . . . . ? C2 N1 C11 C16 -127.9(3) . . . . ? C9A N1 C11 C12 -130.4(3) . . . . ? C2 N1 C11 C12 52.3(3) . . . . ? N4 C3A C3 C30 -0.8(4) . . . . ? C9A C3A C3 C30 178.8(2) . . . . ? N4 C3A C3 C2 178.5(2) . . . . ? C9A C3A C3 C2 -1.9(3) . . . . ? O2 C2 C3 C30 1.1(4) . . . . ? N1 C2 C3 C30 -179.8(2) . . . . ? O2 C2 C3 C3A -178.2(3) . . . . ? N1 C2 C3 C3A 0.9(3) . . . . ? C30 N30 C37 C38 135.0(3) . . . . ? C32 C31 C36 C35 0.6(3) . . . . ? C30 C31 C36 C35 -178.8(2) . . . . ? C37 N30 C30 C3 -175.8(2) . . . . ? C37 N30 C30 C31 1.8(4) . . . . ? C3A C3 C30 N30 11.5(4) . . . . ? C2 C3 C30 N30 -167.7(2) . . . . ? C3A C3 C30 C31 -166.1(2) . . . . ? C2 C3 C30 C31 14.7(4) . . . . ? C32 C31 C30 N30 60.2(3) . . . . ? C36 C31 C30 N30 -120.4(3) . . . . ? C32 C31 C30 C3 -122.3(3) . . . . ? C36 C31 C30 C3 57.1(3) . . . . ? C15 C14 C13 C12 -0.4(4) . . . . ? C8A C8 C7 C6 -1.7(4) . . . . ? N5 C6 C7 C8 -0.8(4) . . . . ? C12 C11 C16 C15 0.0(4) . . . . ? N1 C11 C16 C15 -179.8(2) . . . . ? C16 C11 C12 C13 0.3(4) . . . . ? N1 C11 C12 C13 -179.9(2) . . . . ? C14 C13 C12 C11 -0.1(4) . . . . ? C36 C31 C32 C33 -1.4(3) . . . . ? C30 C31 C32 C33 178.0(2) . . . . ? C31 C32 C33 C34 0.9(4) . . . . ? C31 C36 C35 C34 0.7(4) . . . . ? C13 C14 C15 C16 0.8(4) . . . . ? C11 C16 C15 C14 -0.6(4) . . . . ? C36 C35 C34 C33 -1.3(4) . . . . ? C32 C33 C34 C35 0.5(4) . . . . ? O39 C39 C38 C37 -66.0(3) . . . . ? N30 C37 C38 C39 156.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N30 H30 N4 0.85(3) 2.16(3) 2.837(3) 137(3) . N30 H30 O1W 0.85(3) 2.65(3) 3.199(4) 124(2) . O1W H2W O39 0.916(19) 2.08(2) 2.973(4) 164(4) . O39 H39 N5 0.88(2) 1.87(2) 2.745(3) 173(5) 2_545 O1W H1W O39 0.906(19) 1.92(3) 2.794(4) 161(4) 2 # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 890198' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_new2 #TrackingRef '12376_web_deposit_cif_file_0_JustynaKalinowska-Tluscik_1341322378.ccdc_deposit_OK2_KO1.cif' _audit_creation_date 2012-06-26T16:46:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (E)-1-benzyl-3-[(3-hydroxypropylamino)-phenylmethylidene]-1,3-dihydro-2H- pyrido[2,3-b]pyrrolo[3,2-e]pyrazin-2-one- pyrido[3,4-b]pyrrolo[3,2-e]pyrazin-2-one ; _chemical_formula_moiety 'C26 H23 N5 O2' _chemical_formula_sum 'C26 H23 N5 O2' _chemical_formula_weight 437.49 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.1766(1) _cell_length_b 11.1148(1) _cell_length_c 21.7846(2) _cell_angle_alpha 90 _cell_angle_beta 106.341(1) _cell_angle_gamma 90 _cell_volume 2132.19(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.75197 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3756 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_unetI/netI 0.0224 _diffrn_reflns_number 32725 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.9 _diffrn_reflns_theta_max 28.5 _diffrn_reflns_theta_full 28.5 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 5395 _reflns_number_gt 4494 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+0.9399P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5395 _refine_ls_number_parameters 323 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.362 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.045 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.42106(10) 0.31839(8) 0.36151(4) 0.0241(2) Uani 1 1 d . . . N4 N 0.82950(11) 0.60008(9) 0.43785(4) 0.0165(2) Uani 1 1 d . . . N9 N 0.75108(11) 0.48242(9) 0.54425(5) 0.0176(2) Uani 1 1 d . . . O39 O 1.12875(10) 0.73551(9) 0.25998(4) 0.0245(2) Uani 1 1 d . . . N1 N 0.57149(11) 0.37894(9) 0.46065(5) 0.0173(2) Uani 1 1 d . . . N30 N 0.72416(11) 0.57213(10) 0.30034(5) 0.0195(2) Uani 1 1 d . B . C3A C 0.72169(12) 0.51841(10) 0.43030(5) 0.0154(2) Uani 1 1 d . . . C5 C 1.02017(13) 0.71273(11) 0.51683(6) 0.0186(2) Uani 1 1 d . . . H5 H 1.0519 0.7517 0.484 0.022 Uiso 1 1 calc R . . C4A C 0.90215(13) 0.62709(10) 0.50129(5) 0.0164(2) Uani 1 1 d . . . C8 C 0.93884(14) 0.60633(11) 0.61549(6) 0.0208(2) Uani 1 1 d . . . H8 H 0.9102 0.5697 0.6498 0.025 Uiso 1 1 calc R . . N7 N 1.04866(12) 0.68789(10) 0.62979(5) 0.0221(2) Uani 1 1 d . . . C8A C 0.86209(13) 0.57063(11) 0.55284(5) 0.0173(2) Uani 1 1 d . . . C9A C 0.68654(12) 0.45954(10) 0.48432(5) 0.0158(2) Uani 1 1 d . . . C10 C 0.51200(13) 0.29517(11) 0.49922(6) 0.0195(2) Uani 1 1 d . . . H10A H 0.4119 0.2649 0.4736 0.023 Uiso 1 1 calc R . . H10B H 0.4969 0.3382 0.5368 0.023 Uiso 1 1 calc R . . C30 C 0.61741(13) 0.50119(10) 0.31075(5) 0.0160(2) Uani 1 1 d . . . C11 C 0.61764(13) 0.18992(11) 0.52190(5) 0.0178(2) Uani 1 1 d . . . C3 C 0.61913(13) 0.47172(10) 0.37335(5) 0.0165(2) Uani 1 1 d . . . C2 C 0.52290(13) 0.38222(11) 0.39276(5) 0.0179(2) Uani 1 1 d . . . C31 C 0.49445(13) 0.45767(10) 0.25465(5) 0.0166(2) Uani 1 1 d . . . C16 C 0.70770(14) 0.18500(11) 0.58508(6) 0.0205(2) Uani 1 1 d . . . H16 H 0.7024 0.2479 0.6139 0.025 Uiso 1 1 calc R . . C6 C 1.08892(14) 0.73928(11) 0.58008(6) 0.0209(2) Uani 1 1 d . . . H6 H 1.1689 0.7966 0.5896 0.025 Uiso 1 1 calc R . . C37 C 0.72658(14) 0.62235(13) 0.23829(6) 0.0240(3) Uani 1 1 d . . . H37A H 0.6827 0.7044 0.2338 0.029 Uiso 1 1 calc R A 1 H37B H 0.6626 0.572 0.2035 0.029 Uiso 1 1 calc R A 1 C12 C 0.62729(15) 0.09706(12) 0.48015(6) 0.0240(3) Uani 1 1 d . . . H12 H 0.5662 0.0994 0.437 0.029 Uiso 1 1 calc R . . C36 C 0.52046(14) 0.36701(12) 0.21486(6) 0.0216(2) Uani 1 1 d . . . H36 H 0.6177 0.3305 0.2234 0.026 Uiso 1 1 calc R . . C15 C 0.80543(15) 0.08841(12) 0.60620(6) 0.0259(3) Uani 1 1 d . . . H15 H 0.8659 0.0852 0.6494 0.031 Uiso 1 1 calc R . . C33 C 0.23697(14) 0.47645(12) 0.18828(6) 0.0248(3) Uani 1 1 d . . . H33 H 0.1407 0.5149 0.1786 0.03 Uiso 1 1 calc R . . C32 C 0.35240(14) 0.51272(11) 0.24138(6) 0.0212(2) Uani 1 1 d . . . H32 H 0.3346 0.5746 0.2685 0.025 Uiso 1 1 calc R . . C14 C 0.81477(17) -0.00322(13) 0.56428(7) 0.0296(3) Uani 1 1 d . . . H14 H 0.882 -0.0689 0.5786 0.036 Uiso 1 1 calc R . . C35 C 0.40315(15) 0.33018(13) 0.16249(6) 0.0258(3) Uani 1 1 d . . . H35 H 0.42 0.2676 0.1356 0.031 Uiso 1 1 calc R . . C13 C 0.72551(17) 0.00144(12) 0.50135(7) 0.0301(3) Uani 1 1 d . . . H13 H 0.7317 -0.0613 0.4726 0.036 Uiso 1 1 calc R . . C34 C 0.26159(15) 0.38450(13) 0.14947(6) 0.0257(3) Uani 1 1 d . . . H34 H 0.1815 0.3586 0.1139 0.031 Uiso 1 1 calc R . . H39 H 1.1097(18) 0.7585(15) 0.2192(8) 0.031 Uiso 1 1 d . . . H30 H 0.7921(18) 0.6015(15) 0.3353(8) 0.031 Uiso 1 1 d . . . C38A C 0.88656(16) 0.62799(15) 0.23144(7) 0.0186(3) Uani 0.88 1 d P B 1 H38A H 0.8806 0.6433 0.186 0.022 Uiso 0.88 1 calc PR B 1 H38B H 0.9358 0.5488 0.2431 0.022 Uiso 0.88 1 calc PR B 1 C39A C 0.98565(16) 0.72466(16) 0.27256(7) 0.0200(3) Uani 0.88 1 d P B 1 H39A H 0.9321 0.8029 0.2643 0.024 Uiso 0.88 1 calc PR B 1 H39B H 1.0018 0.7047 0.3183 0.024 Uiso 0.88 1 calc PR B 1 C38B C 0.856(2) 0.6918(17) 0.2367(7) 0.046(3) Uani 0.12 1 d PU B 2 H38C H 0.8477 0.7058 0.191 0.055 Uiso 0.12 1 calc PR B 2 H38D H 0.8433 0.7713 0.2551 0.055 Uiso 0.12 1 calc PR B 2 C39B C 1.001(2) 0.6581(17) 0.2644(7) 0.048(4) Uani 0.12 1 d PU B 2 H39C H 1.0153 0.5787 0.2464 0.057 Uiso 0.12 1 calc PR B 2 H39D H 1.0114 0.6455 0.3105 0.057 Uiso 0.12 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0255(5) 0.0260(5) 0.0198(4) -0.0011(3) 0.0050(4) -0.0083(4) N4 0.0160(4) 0.0183(5) 0.0148(4) 0.0009(4) 0.0036(4) 0.0023(4) N9 0.0172(5) 0.0203(5) 0.0154(4) 0.0014(4) 0.0049(4) 0.0024(4) O39 0.0182(4) 0.0369(5) 0.0183(4) 0.0023(4) 0.0048(3) -0.0029(4) N1 0.0176(5) 0.0200(5) 0.0145(4) 0.0030(4) 0.0047(4) -0.0006(4) N30 0.0183(5) 0.0263(5) 0.0127(4) 0.0025(4) 0.0023(4) -0.0042(4) C3A 0.0152(5) 0.0176(5) 0.0136(5) 0.0016(4) 0.0043(4) 0.0036(4) C5 0.0169(5) 0.0196(5) 0.0192(5) 0.0004(4) 0.0051(4) 0.0021(4) C4A 0.0158(5) 0.0176(5) 0.0156(5) 0.0000(4) 0.0041(4) 0.0041(4) C8 0.0204(6) 0.0265(6) 0.0154(5) -0.0009(4) 0.0050(4) 0.0028(5) N7 0.0202(5) 0.0269(6) 0.0185(5) -0.0037(4) 0.0043(4) 0.0030(4) C8A 0.0155(5) 0.0202(6) 0.0158(5) 0.0005(4) 0.0040(4) 0.0032(4) C9A 0.0152(5) 0.0166(5) 0.0163(5) 0.0024(4) 0.0055(4) 0.0034(4) C10 0.0181(5) 0.0224(6) 0.0195(5) 0.0062(4) 0.0078(4) 0.0012(4) C30 0.0154(5) 0.0172(5) 0.0153(5) 0.0009(4) 0.0041(4) 0.0029(4) C11 0.0176(5) 0.0187(5) 0.0186(5) 0.0034(4) 0.0077(4) -0.0012(4) C3 0.0159(5) 0.0184(5) 0.0153(5) 0.0014(4) 0.0042(4) 0.0002(4) C2 0.0185(5) 0.0201(6) 0.0154(5) 0.0016(4) 0.0052(4) 0.0022(4) C31 0.0168(5) 0.0197(5) 0.0130(5) 0.0023(4) 0.0034(4) -0.0015(4) C16 0.0251(6) 0.0199(6) 0.0173(5) 0.0010(4) 0.0074(5) 0.0004(5) C6 0.0177(5) 0.0221(6) 0.0223(6) -0.0033(5) 0.0047(5) 0.0015(5) C37 0.0218(6) 0.0344(7) 0.0146(5) 0.0065(5) 0.0033(4) -0.0055(5) C12 0.0293(6) 0.0251(6) 0.0173(6) -0.0003(5) 0.0062(5) -0.0016(5) C36 0.0194(6) 0.0256(6) 0.0205(6) -0.0019(5) 0.0068(5) 0.0002(5) C15 0.0293(6) 0.0272(7) 0.0196(6) 0.0049(5) 0.0044(5) 0.0048(5) C33 0.0162(5) 0.0296(7) 0.0261(6) 0.0064(5) 0.0020(5) -0.0006(5) C32 0.0199(6) 0.0222(6) 0.0216(6) -0.0004(5) 0.0058(5) 0.0007(5) C14 0.0347(7) 0.0253(7) 0.0304(7) 0.0055(5) 0.0116(6) 0.0100(6) C35 0.0282(6) 0.0319(7) 0.0190(6) -0.0062(5) 0.0097(5) -0.0065(5) C13 0.0433(8) 0.0243(7) 0.0257(7) -0.0033(5) 0.0148(6) 0.0037(6) C34 0.0225(6) 0.0372(7) 0.0156(5) 0.0013(5) 0.0026(5) -0.0095(5) C38A 0.0217(7) 0.0209(7) 0.0141(6) -0.0026(6) 0.0065(5) -0.0041(6) C39A 0.0199(7) 0.0243(8) 0.0175(6) -0.0052(6) 0.0078(5) -0.0057(6) C38B 0.078(9) 0.040(9) 0.029(7) -0.006(6) 0.029(7) -0.018(8) C39B 0.081(10) 0.039(9) 0.030(7) -0.008(6) 0.026(7) -0.028(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C2 1.2175(15) . ? N4 C3A 1.3184(15) . ? N4 C4A 1.3879(14) . ? N9 C9A 1.2979(15) . ? N9 C8A 1.3880(15) . ? O39 C39A 1.4200(16) . ? O39 C39B 1.481(15) . ? O39 H39 0.893(17) . ? N1 C9A 1.3698(15) . ? N1 C2 1.4200(14) . ? N1 C10 1.4591(14) . ? N30 C30 1.3257(15) . ? N30 C37 1.4684(15) . ? N30 H30 0.899(17) . ? C3A C3 1.4273(15) . ? C3A C9A 1.4598(15) . ? C5 C6 1.3763(16) . ? C5 C4A 1.4097(16) . ? C5 H5 0.95 . ? C4A C8A 1.4221(16) . ? C8 N7 1.3258(16) . ? C8 C8A 1.4054(16) . ? C8 H8 0.95 . ? N7 C6 1.3641(16) . ? C10 C11 1.5110(16) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C30 C3 1.3983(15) . ? C30 C31 1.4915(15) . ? C11 C16 1.3929(16) . ? C11 C12 1.3949(17) . ? C3 C2 1.4691(16) . ? C31 C36 1.3930(17) . ? C31 C32 1.3947(16) . ? C16 C15 1.3916(17) . ? C16 H16 0.95 . ? C6 H6 0.95 . ? C37 C38B 1.424(16) . ? C37 C38A 1.5181(19) . ? C37 H37A 0.99 . ? C37 H37B 0.99 . ? C12 C13 1.3859(19) . ? C12 H12 0.95 . ? C36 C35 1.3918(17) . ? C36 H36 0.95 . ? C15 C14 1.3867(19) . ? C15 H15 0.95 . ? C33 C34 1.3849(19) . ? C33 C32 1.3903(17) . ? C33 H33 0.95 . ? C32 H32 0.95 . ? C14 C13 1.3860(19) . ? C14 H14 0.95 . ? C35 C34 1.3875(19) . ? C35 H35 0.95 . ? C13 H13 0.95 . ? C34 H34 0.95 . ? C38A C39A 1.525(2) . ? C38A H38A 0.99 . ? C38A H38B 0.99 . ? C39A H39A 0.99 . ? C39A H39B 0.99 . ? C38B C39B 1.35(3) . ? C38B H38C 0.99 . ? C38B H38D 0.99 . ? C39B H39C 0.99 . ? C39B H39D 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3A N4 C4A 113.99(10) . . ? C9A N9 C8A 112.58(10) . . ? C39A O39 C39B 31.2(8) . . ? C39A O39 H39 106.4(10) . . ? C39B O39 H39 107.1(12) . . ? C9A N1 C2 110.99(9) . . ? C9A N1 C10 125.04(10) . . ? C2 N1 C10 123.87(10) . . ? C30 N30 C37 125.93(10) . . ? C30 N30 H30 116.1(10) . . ? C37 N30 H30 117.1(10) . . ? N4 C3A C3 130.31(10) . . ? N4 C3A C9A 122.43(10) . . ? C3 C3A C9A 107.25(10) . . ? C6 C5 C4A 119.34(11) . . ? C6 C5 H5 120.3 . . ? C4A C5 H5 120.3 . . ? N4 C4A C5 120.43(10) . . ? N4 C4A C8A 122.17(10) . . ? C5 C4A C8A 117.40(10) . . ? N7 C8 C8A 124.15(11) . . ? N7 C8 H8 117.9 . . ? C8A C8 H8 117.9 . . ? C8 N7 C6 117.23(10) . . ? N9 C8A C8 118.60(10) . . ? N9 C8A C4A 123.24(10) . . ? C8 C8A C4A 118.16(11) . . ? N9 C9A N1 126.30(10) . . ? N9 C9A C3A 125.54(11) . . ? N1 C9A C3A 108.14(10) . . ? N1 C10 C11 111.89(9) . . ? N1 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? N1 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N30 C30 C3 120.00(10) . . ? N30 C30 C31 118.55(10) . . ? C3 C30 C31 121.42(10) . . ? C16 C11 C12 119.11(11) . . ? C16 C11 C10 120.08(11) . . ? C12 C11 C10 120.81(11) . . ? C30 C3 C3A 125.89(10) . . ? C30 C3 C2 126.63(10) . . ? C3A C3 C2 107.38(9) . . ? O2 C2 N1 122.29(11) . . ? O2 C2 C3 131.50(11) . . ? N1 C2 C3 106.21(10) . . ? C36 C31 C32 120.14(11) . . ? C36 C31 C30 121.46(10) . . ? C32 C31 C30 118.37(10) . . ? C15 C16 C11 120.33(11) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? N7 C6 C5 123.69(11) . . ? N7 C6 H6 118.2 . . ? C5 C6 H6 118.2 . . ? C38B C37 N30 117.2(6) . . ? C38B C37 C38A 30.7(8) . . ? N30 C37 C38A 111.82(10) . . ? C38B C37 H37A 79.5 . . ? N30 C37 H37A 109.3 . . ? C38A C37 H37A 109.3 . . ? C38B C37 H37B 127.4 . . ? N30 C37 H37B 109.3 . . ? C38A C37 H37B 109.3 . . ? H37A C37 H37B 107.9 . . ? C13 C12 C11 120.32(12) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C35 C36 C31 119.63(11) . . ? C35 C36 H36 120.2 . . ? C31 C36 H36 120.2 . . ? C14 C15 C16 120.16(12) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C34 C33 C32 120.33(12) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C32 C31 119.61(12) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C15 C14 C13 119.68(12) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C34 C35 C36 120.22(12) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C14 C13 C12 120.41(12) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C33 C34 C35 120.04(12) . . ? C33 C34 H34 120 . . ? C35 C34 H34 120 . . ? C37 C38A C39A 113.87(13) . . ? C37 C38A H38A 108.8 . . ? C39A C38A H38A 108.8 . . ? C37 C38A H38B 108.8 . . ? C39A C38A H38B 108.8 . . ? H38A C38A H38B 107.7 . . ? O39 C39A C38A 112.18(13) . . ? O39 C39A H39A 109.2 . . ? C38A C39A H39A 109.2 . . ? O39 C39A H39B 109.2 . . ? C38A C39A H39B 109.2 . . ? H39A C39A H39B 107.9 . . ? C39B C38B C37 124.2(15) . . ? C39B C38B H38C 106.3 . . ? C37 C38B H38C 106.3 . . ? C39B C38B H38D 106.3 . . ? C37 C38B H38D 106.3 . . ? H38C C38B H38D 106.4 . . ? C38B C39B O39 120.6(15) . . ? C38B C39B H39C 107.2 . . ? O39 C39B H39C 107.2 . . ? C38B C39B H39D 107.2 . . ? O39 C39B H39D 107.2 . . ? H39C C39B H39D 106.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4A N4 C3A C3 177.00(11) . . . . ? C4A N4 C3A C9A -1.91(15) . . . . ? C3A N4 C4A C5 179.90(10) . . . . ? C3A N4 C4A C8A 0.00(15) . . . . ? C6 C5 C4A N4 179.03(10) . . . . ? C6 C5 C4A C8A -1.07(16) . . . . ? C8A C8 N7 C6 -0.27(18) . . . . ? C9A N9 C8A C8 178.53(10) . . . . ? C9A N9 C8A C4A -1.37(15) . . . . ? N7 C8 C8A N9 178.72(11) . . . . ? N7 C8 C8A C4A -1.38(18) . . . . ? N4 C4A C8A N9 1.78(17) . . . . ? C5 C4A C8A N9 -178.12(10) . . . . ? N4 C4A C8A C8 -178.11(10) . . . . ? C5 C4A C8A C8 1.99(16) . . . . ? C8A N9 C9A N1 -178.71(10) . . . . ? C8A N9 C9A C3A -0.60(16) . . . . ? C2 N1 C9A N9 176.69(11) . . . . ? C10 N1 C9A N9 -6.82(18) . . . . ? C2 N1 C9A C3A -1.69(12) . . . . ? C10 N1 C9A C3A 174.80(10) . . . . ? N4 C3A C9A N9 2.43(18) . . . . ? C3 C3A C9A N9 -176.69(11) . . . . ? N4 C3A C9A N1 -179.17(10) . . . . ? C3 C3A C9A N1 1.70(12) . . . . ? C9A N1 C10 C11 -75.79(14) . . . . ? C2 N1 C10 C11 100.26(13) . . . . ? C37 N30 C30 C3 -172.06(11) . . . . ? C37 N30 C30 C31 6.00(18) . . . . ? N1 C10 C11 C16 103.91(12) . . . . ? N1 C10 C11 C12 -75.70(14) . . . . ? N30 C30 C3 C3A 4.94(18) . . . . ? C31 C30 C3 C3A -173.06(11) . . . . ? N30 C30 C3 C2 -171.03(11) . . . . ? C31 C30 C3 C2 10.97(18) . . . . ? N4 C3A C3 C30 3.3(2) . . . . ? C9A C3A C3 C30 -177.68(11) . . . . ? N4 C3A C3 C2 179.90(11) . . . . ? C9A C3A C3 C2 -1.07(12) . . . . ? C9A N1 C2 O2 -179.62(11) . . . . ? C10 N1 C2 O2 3.84(18) . . . . ? C9A N1 C2 C3 1.01(13) . . . . ? C10 N1 C2 C3 -175.53(10) . . . . ? C30 C3 C2 O2 -2.6(2) . . . . ? C3A C3 C2 O2 -179.20(12) . . . . ? C30 C3 C2 N1 176.66(11) . . . . ? C3A C3 C2 N1 0.09(12) . . . . ? N30 C30 C31 C36 75.33(15) . . . . ? C3 C30 C31 C36 -106.64(14) . . . . ? N30 C30 C31 C32 -102.63(13) . . . . ? C3 C30 C31 C32 75.40(15) . . . . ? C12 C11 C16 C15 -0.26(18) . . . . ? C10 C11 C16 C15 -179.87(11) . . . . ? C8 N7 C6 C5 1.31(18) . . . . ? C4A C5 C6 N7 -0.61(18) . . . . ? C30 N30 C37 C38B -176.8(9) . . . . ? C30 N30 C37 C38A -143.56(13) . . . . ? C16 C11 C12 C13 -0.14(18) . . . . ? C10 C11 C12 C13 179.47(12) . . . . ? C32 C31 C36 C35 -1.18(18) . . . . ? C30 C31 C36 C35 -179.10(11) . . . . ? C11 C16 C15 C14 0.6(2) . . . . ? C34 C33 C32 C31 1.35(19) . . . . ? C36 C31 C32 C33 0.09(18) . . . . ? C30 C31 C32 C33 178.08(11) . . . . ? C16 C15 C14 C13 -0.5(2) . . . . ? C31 C36 C35 C34 0.83(19) . . . . ? C15 C14 C13 C12 0.1(2) . . . . ? C11 C12 C13 C14 0.2(2) . . . . ? C32 C33 C34 C35 -1.70(19) . . . . ? C36 C35 C34 C33 0.6(2) . . . . ? C38B C37 C38A C39A 34.8(12) . . . . ? N30 C37 C38A C39A -72.00(16) . . . . ? C39B O39 C39A C38A -33.3(12) . . . . ? C37 C38A C39A O39 -173.92(11) . . . . ? N30 C37 C38B C39B 46.6(19) . . . . ? C38A C37 C38B C39B -40.7(15) . . . . ? C37 C38B C39B O39 179.5(10) . . . . ? C39A O39 C39B C38B 47.2(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N30 H30 N4 0.899(17) 2.162(17) 2.8939(14) 138.0(14) . O39 H39 N7 0.893(17) 1.962(18) 2.8524(13) 174.7(15) 4_575 _database_code_depnum_ccdc_archive 'CCDC 890197'